Book Holiday Homes in South Kent

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Featured Holiday Homes in South Kent

Lakehouse Boat Dock, Kayaks, Fire-Pit, Pool Table, Air Hockey, Hammock, King Bed

Lakehouse Boat Dock, Kayaks, Fire-Pit, Pool Table, Air Hockey, Hammock, King Bed

New Fairfield CT
Located in New Fairfield, this vacation home is within a 5-minute drive of Candlewood Lake and Squantz Pond State Park.
Opens in a new windowLakehouse Boat Dock, Kayaks, Fire-Pit, Pool Table, Air Hockey, Hammock, King Bed
Lakehouse, Boat Dock, Kayaks, Fire-Pit, King Bed, 1 Hour & 15 Min from NYC etc!

Lakehouse, Boat Dock, Kayaks, Fire-Pit, King Bed, 1 Hour & 15 Min from NYC etc!

New Fairfield CT
Located in New Fairfield, this vacation home is in the mountains, within a 5-minute drive of Candlewood Lake and Squantz Pond State Park.
Opens in a new windowLakehouse, Boat Dock, Kayaks, Fire-Pit, King Bed, 1 Hour & 15 Min from NYC etc!
Candlewood Lake - Family Getaway with direct lake access. 3775 sqft home.

Candlewood Lake - Family Getaway with direct lake access. 3775 sqft home.

Danbury CT
Located in Danbury, this vacation home is on the waterfront, within a 10-minute drive of Candlewood Lake and Hatters Park.
Opens in a new windowCandlewood Lake - Family Getaway with direct lake access. 3775 sqft home.
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Charming Home with Fireplace and Indoor Pool in Sharon, CT

Charming Home with Fireplace and Indoor Pool in Sharon, CT

Sharon CT
Located in Sharon, this vacation home is in a rural location, a 4-minute drive from Bodhi Tree Gallery and 6 minutes from TriArts Sharon Playhouse.
Opens in a new windowCharming Home with Fireplace and Indoor Pool in Sharon, CT
Candlewood Lake Retreat; Dock, Game Room & Firepit

Candlewood Lake Retreat; Dock, Game Room & Firepit

New Milford CT
With a stay at this vacation home in New Milford, you'll be on the waterfront, just steps from Candlewood Lake and a 3-minute drive from Elephant's Trunk Flea ...
Opens in a new windowCandlewood Lake Retreat; Dock, Game Room & Firepit
Peaceful & Quiet Lakeside Home with Hot Tub, Pool Table, Fire Pit

Peaceful & Quiet Lakeside Home with Hot Tub, Pool Table, Fire Pit

Holmes NY
With a stay at this vacation home in Holmes, you'll be on a lake, just steps from Lake Dutchess and a 5-minute drive from Whaley Lake.
Opens in a new windowPeaceful & Quiet Lakeside Home with Hot Tub, Pool Table, Fire Pit
Cozy Lakefront Bungalow w firepit/dock/kayaks

Cozy Lakefront Bungalow w firepit/dock/kayaks

Plymouth CT
Located in Plymouth, this vacation home is on the waterfront, within a 15-minute drive of Black Rock State Park and Rockwell Park.
Opens in a new windowCozy Lakefront Bungalow w firepit/dock/kayaks
Cozy Candlewood Lake Cabin — Family + Friend Retreat

Cozy Candlewood Lake Cabin — Family + Friend Retreat

Danbury CT
When you stay at this vacation home in Danbury, you'll be on a lake, within a 5-minute drive of Candlewood Lake and Candlewood Plaza Shopping Center.
Opens in a new windowCozy Candlewood Lake Cabin — Family + Friend Retreat
Tranquil 4-bedroom house in welcoming Poughquag neighborhood

Tranquil 4-bedroom house in welcoming Poughquag neighborhood

Poughquag NY
The price is AU$484 per night from 30 Mar to 31 Mar
AU$484
30 Mar - 31 Mar
includes taxes & fees
Located in Poughquag, this vacation home is a 4-minute drive from Stormville Airport Antique Show & Flea Market and 6 minutes from Towne Center Park.
Opens in a new windowTranquil 4-bedroom house in welcoming Poughquag neighborhood
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Lowest nightly price found within the past 24 hours based on a 1 night stay for 2 adults. Prices and availability subject to change. Additional terms may apply.

South Kent Holiday Houses

Do you love last minute road trips and late-night food runs and sunrises on the beach? Do words like “schedule” and “calendar” make you shout, “Don’t box me in!”? You might be a little bit of a rebel. But you’re a rebel with a cause: having a smashing holiday. Itinerary? What’s that? Our South Kent vacation homes are the perfect way for you to wing it.

Holiday houses in South Kent let you live life on your own terms. You’ll have so much space, you’ll wish you had more friends and family—but you can always invite over the neighbours. You can often have luxury amenities, but with all the attractions of South Kent in your backyard, budget holiday homes will do just fine, too. That will just leave you more dough to spend on the important things: cocktails, brunch, and local South Kent adventures, obvs.

If your adventure buddy happens to have fur and four legs, you just might find a pet-friendly holiday house in South Kent with your name on it.

No need to spend big bickies for a holiday beach house the size of Buckingham Palace—unless you’re really in trouble with bae. We’ve got a great selection of South Kent vacation homes with everything you need for a seriously amazing getaway. Throw out that daily planner and hit “reject” on all those meeting invites. You’re off to a place where there are no rules.

South Kent Holiday Homes essential information

Accommodation
226 Holiday Homes
Lowest Price
AU$138
Highest Price
AU$484
Popular accommodation
Lakehouse Boat Dock, Kayaks, Fire-Pit, Pool Table, Air Hockey, Hammock, King Bed, Lakehouse, Boat Dock, Kayaks, Fire-Pit, King Bed, 1 Hour & 15 Min from NYC etc!, Candlewood Lake - Family Getaway with direct lake access. 3775 sqft home., Charming Home with Fireplace and Indoor Pool in Sharon, CT, Candlewood Lake Retreat; Dock, Game Room & Firepit, Peaceful & Quiet Lakeside Home with Hot Tub, Pool Table, Fire Pit, Cozy Lakefront Bungalow w firepit/dock/kayaks, Cozy Candlewood Lake Cabin — Family + Friend Retreat, Tranquil 4-bedroom house in welcoming Poughquag neighborhood

Top trending hotels in South Kent

Best Western Danbury/Bethel

Best Western Danbury/Bethel

2.5 out of 5
11 Stony Hill Road Bethel CT
Fully refundableReserve now, pay when you stay
The price is AU$138 per night from 26 Apr to 27 Apr
AU$138
26 Apr - 27 Apr
includes taxes & fees
With a stay at Best Western Danbury/Bethel in Bethel, you'll be near the airport, just steps from The Cave and a 2-minute drive from Still River Greenway.
Opens in a new windowBest Western Danbury/Bethel
Heritage Hotel, Golf & Conference Center

Heritage Hotel, Golf & Conference Center

3.5 out of 5
522 Heritage Road Southbury CT
Fully refundableReserve now, pay when you stay
The price is AU$225 per night from 30 Mar to 31 Mar
AU$225
30 Mar - 31 Mar
includes taxes & fees
With a stay at Heritage Hotel, Golf & Conference Center in Southbury, you'll be near ski lifts, just steps from Vicinanza Studios & Gallery and a 3-minute drive ...
Opens in a new windowHeritage Hotel, Golf & Conference Center
Wyndham Southbury

Wyndham Southbury

3 out of 5
1284 Strongtown Road Southbury CT
Fully refundableReserve now, pay when you stay
The price is AU$169 per night from 5 Apr to 6 Apr
AU$169
5 Apr - 6 Apr
includes taxes & fees
Located in Southbury, Wyndham Southbury is a 4-minute drive from Lake Quassapaug and 5 minutes from Southford Falls State Park.
Opens in a new windowWyndham Southbury
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Hampton Inn Danbury

Hampton Inn Danbury

2.5 out of 5
81 Newtown Rd Danbury CT
Fully refundableReserve now, pay when you stay
The price is AU$231 per night from 5 Apr to 6 Apr
AU$231
5 Apr - 6 Apr
includes taxes & fees
When you stay at Hampton Inn Danbury in Danbury, you'll be in a shopping district, within a 10-minute walk of Still River Greenway and Berkshire Shopping ...
Opens in a new windowHampton Inn Danbury
Don't see what you're looking for?
See all available properties in South Kent
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Lowest nightly price found within the past 24 hours based on a 1 night stay for 2 adults. Prices and availability subject to change. Additional terms may apply.

Top Picks

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^Subject to availability and chosen travel dates.